Ethyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate → 4'-{[4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile

HRID 519527

Reaction equation

HRID 519527 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[C:11]([F:27])[CH:10]=1)#[N:2].[CH3:28][C:29]1([CH3:42])[CH2:34][CH:33]([NH:35][C:36]2[NH:40][C:39]([CH3:41])=[N:38][N:37]=2)[CH2:32][CH2:31][O:30]1>>[CH3:28][C:29]1([CH3:42])[CH2:34][CH:33]([N:35]2[C:17](=[O:18])[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:10][C:11]=3[F:27])=[C:22]([CH2:23][CH2:24][CH3:25])[N:37]3[N:38]=[C:39]([CH3:41])[N:40]=[C:36]23)[CH2:32][CH2:31][O:30]1

Participants

3

Reactant 2

HCID 57460949Ethyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178434104HCID 178434104, compound

Product 1

HCID 670088724'-{[4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrileYield 56%

Conditions

Temperature
250 °C

Procedure

A mixture of ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (0.87 g) and N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5-methyl-4H-1,2,4-triazol-3-amine (0.25 g) was stirred at 250° C. for 20 min under microwave irradiation. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (0.34 g, 56%).

Workup

  1. customThe obtained reaction mixture
  2. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-627bf0dd37af4474a592cdfcb95c537a
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Linked notes

Loading…